Combined Basics of Organic Chemistry Notes

3.
Concepts of Bonding S i r
p t a
Basics of Organic u
Chemistry m G1
p a
n u
A
Anupam Gupta
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What are the common features of the organic compounds?
● All organic compounds contain carbon atoms and most contain hydrogen atoms.
●
S i r
All the carbon atoms have four bonds. A stable carbon atom is said to be
tetravalent.
p t a
G u
a m
u p
A n

What are the common features of the organic compounds?
● Other elements may also be present. Any atom that is not carbon or hydrogen is
i r
called a heteroatom. Common heteroatoms include N, O, S, P and the halogens.
S
●
p t a
Some compounds have chains of atoms and some compounds have rings.
G u
a m
u p
A n

Classification of organic compounds
Organic Compounds
S i r
p t a
Acyclic or open chain or
aliphatic compounds G u Cyclic Compounds
CH3-CH2-CH3(Propane)
a m
u p
A n
Homocyclic compounds Heterocyclic compounds

Valence Electrons
S i r
p t a
G u
a m
u p
A n

Valence Electrons
S i r
p t a
G u
a m
u p
A n

Valence Electrons
S i r
p t a
G u
a m
u p
A n

Keep track of electrons: Formal Charges
A formal charge (FC) is the charge assigned to an atom in a molecule, assuming that
electrons in all chemical bonds are shared equally between atoms
S i r
t a
Formal Charge = [# of valence electrons] – [non-bonded electrons + number of bonds]
p
G u
a m
u p
A n

Formal Charge: +1
S i r
p t a
G u
a m
u p
A n

Formal Charge: +1
S i r
p t a
G u
a m
u p
A n

Formal Charge: -1
S i r
p t a
G u
a m
u p
A n

Calculating Formal Charge
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Lewis Octet Rule: Is the Carbon with +1 Formal Charge Unstable?
S i r
p t a
G u
a m
u p
A n

Lewis Octet Rule: Is the Nitrogen with +1 Formal Charge Unstable?
S i r
p t a
G u
a m
u p
A n

Geometry & Hybridization
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

3.0
Concepts of Bonding-2 S i r
p t a
Basics of Organic u
Chemistry m G2
p a
n u
A
Anupam Gupta
Revision: Formal Charge
S i r
p t a
G u
a m
u p
A n

Revision: Hybridization
S i r
p t a
G u
a m
u p
A n

Select the molecule which has only one π-bond
A. CH ≡ CH
B. CH2 = CHCHO
S i r
C. CH3CH=CH2
p t a
D. CH3CH = CHCOOH
G u
a m
u p
A n

The hybridisation of carbon atom in C - C single bond of
H2C = CH - CH = CH2 is
A. sp3 - sp
S i r
B. sp2 - sp
C. sp2 - sp3
p t a
D. sp3 - sp3
G u
a m
u p
A n

Mixing of Atomic Orbitals for Hybridized Orbitals
S i r
Hybridization
p t a
G u
s Character
a m
u p
A n

Mixing of Atomic Orbitals for Hybridized Orbitals -s & p orbital
S i r
p t a
G u
a m
u p
A n

In 2sp hybridization, 2s-orbital can be mixed with
A. Only 2px
B. Only 2py
S i r
C. Only 2pz
p t a
D. Any one of 2px, 2py and 2pz
G u
a m
u p
A n

Mixing of Atomic Orbitals for Hybridized Orbitals
S i r
p t a
G u
a m
u p
A n

The percentage of s- character of the hybrid orbitals in ethane, ethene
and ethyne are respectively.
A. 50, 75,100
S i r
B. 10, 20, 40
C. 25, 33, 50
p t a
D. 25, 50, 75
G u
a m
u p
A n

In 2sp2 orbital, character of 2pz orbital will be
A. Always 33.33%
B. Always 0%
S i r
C. Always 66.66%
p t a
D. Either 33.33% or 0%
G u
a m
u p
A n

Energy of Hybridized Orbitals
The s orbital is closer to the nucleus and thus lower in energy than the p orbital
S i r
Hybridized orbitals are degenerate i.e. they occupy the same energy level; however,
p t a
they are higher in energy than the 2s orbital and lower in energy than the 2p orbital.
G u
Just like any other atomic orbital, each sp3 hybrid orbital can house 2 electrons.
a m
u p
A n

Which of the following statements about the energy of hybrid or from
mixing of 2s and 2p orbitals is true?
A. E2p > Esp3 > Esp2 > Esp > E2s

S i r
B. Esp3 > Esp2 > Esp > E2p > E2s
C. E2p > Esp > Esp2 > Esp3 > E2s
p t a
D. E2p > Esp > E2s > Esp2 > Esp3
G u
a m
u p
A n

Size of Hybridized Orbitals
S i r
p t a
G u
a m
u p
A n

Which of the following statements about the size of hybrid orbitals
resulting from mixing of 2s and 2p orbitals is true?
A. 2s > 2p sp3 > sp2 > sp

S i r
B. 2p > 2s > sp3 > sp2 > sp
C. 2p > sp3 > sp2 > sp > 2s
p t a
D. Sp3 > sp2 > sp > 2p > 2s
G u
a m
u p
A n

Which of the following orders is correct for electronegativity?
A. sp3C > sp2C > spC

B. spC > sp2C > sp3C
S i r
C. sp2C > spC > sp3C
p t a
D. sp3C > spC > sp2C
G u
a m
u p
A n

S-character and the stability of the anion
The closer the electrons are to the nucleus, the more stable they are. Therefore, when
i r
bearing the negative charge, sp3 species are less stable than sp2 and sp species.
S
p t a
G u
a m
u p
A n

Bond length and bond strength
The greater the s-character, the closer the electrons are held to the nucleus, the shorter
i r
the bond, and the stronger the bond. Thus, sp3 hybridized atoms form longer and weaker
bonds than those of sp2 and sp hybridized.
S
p t a
G u
a m
u p
A n

The orbitals used by C in forming C-H and C-Cl bonds of CH2Cl2 are
A. Four sp orbitals
B. Four sp2 orbitals
S i r
C. Four sp3 orbitals
p t a
D. None of these
G u
a m
u p
A n

CH2 = C = CH3
In this molecule (allene)
A. all three C-atoms are sp2 hybridized

S i r
hybridized
p t a
B. both terminal C-atoms are sp2 hybridized while central C-atom is sp-
u
C. both terminal C-atoms are sp-hybridized while central C-atom is sp2
G
hybridized
D. none of these a m
u p
A n

Which of the following compounds has maximum number of sp-
hybridized C-atoms?
A. (CN)2
S i r
B. CH ≡ C -CN
C. HC ≡ C-CH2-CH = C = C = CH2
p t a
D. CH2 = C = CH - CN
G u
a m
u p
A n

CH3 - O -CH = CH2
Oxygen atom of this molecular structure is
A. sp3 hybridized
S i r
B. sp2 hybridized
C. sp-hybridized
p t a
D. unhybridized
G u
a m
u p
A n

Planarity of atoms
S i r
p t a
G u
a m
u p
A n

Planarity of atoms
S i r
p t a
G u
a m
u p
A n

In which of the following molecules, all atoms can be coplanar?
S i r
A. B.
p t a
G u
C. D.
a m
u p
A n

Calculated vs Observed Bond Angles in sp3 hybridization
S i r
p t a
G u
a m
u p
A n

Which of the following is the correct order of bond angles?
A. NH3 > H2O > CH4

B. H2O > NH3 > CH4
S i r
C. CH4 > NH3 > H2O
p t a
D. CH4 > H2O > NH3
G u
a m
u p
A n

Which of the following is the correct order of bond angles?
A.
B. S i r
C.
p t a
D.
G u
a m
u p
A n

Free Rotation about the Single Bond
S i r
p t a
G u
a m
u p
A n

Free Rotation about the Single Bond
S i r
p t a
G u
a m
u p
A n

Restricted Rotation about the double bond
Rotation about single bonds is allowed, but double bonds are rigid and cannot be twisted.
S i r
p t a
G u
a m
u p
A n

3.0
i r
Resonance a S
Basics of Organic p t
G u3
Chemistry m
p a
n u
A
Anupam Gupta
Valence Bond Theory
In V.B.T it is assumed that bonded atoms share electron pair equally in covalent bonding.
The number of bonds formed between bonded atoms must be integral always.
S i r
p t a
G u
a m
u p
A n

Experimental data - Fractional Bond Order
Type of bond
O-O oxygen-oxygen single bond

Length in picometers
148 S i r
O=O oxygen-oxygen double bond 121
p t a
Oxygen-Oxygen bond in OZONE
G u
128
a m
u p
A n

Modification of Valence Bond Theory: Resonance
It is possible, however, to explain properly the properties of many species in terms
i r
of a combination or average of two or more valence bond (Lewis) structures.
S
Consider the Ozone Molecule:
p t a
G u
a m
u p
A n

Arrow movement for resonating structures:
S i r
p t a
G u
a m
u p
A n

Consider the carbonate ion:
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Consider the Benzene molecule:
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Resonance Structures
● Resonating structures/ Canonical structures are imaginary. There is ONLY ONE REAL
S i r
STRUCTURE for each molecule or ion. This real structure (the resonance hybrid) takes
p t a
its character from the average of all the individual resonance contributors. The
resonance hybrid is more stable than any individual resonance structures.
G u
a m
u p
A n

● All resonance contributors must have the same molecular formula, the same number of
electrons, and same net charge.
S i r
●
● p a
Resonance contributors only differ by the positions of pi bond and lone pair electrons.
t
Arrow movements does not depict reality. Electrons don’t keep jumping.
G u
a m
u p
A n

Resonance involves
A. Change in the positions of atoms

B. Change in the positions of both σ and π electrons
C. Change in the positions of only π electrons S i r
p
D. Change in the positions of only σ electrons t a
G u
a m
u p
A n

S i r
p t a
G u
Among these, which are canonical structures?
A. I and II
a m
B. I and III
u p
C. II and III
D. all A n

● All resonance contributors must be correct Lewis structures. Each atom should have a
S i r
complete valence shell and be shown with correct formal charges. A carbocation
rules. p t a
(carbon with only 6 valence electrons) is the only allowed exception to the valence shell
G u
a m
u p
A n

S i r
p t a
G u
Which of these structures is not valid canonical structure?
a m
A. I
B. II u p
C. III
A n
D. None of these

S i r
p t a
G u
Which of these structures is not valid canonical structure of
nitromethane?
a m
A. I
B. II u p
C. III
A n
D. None of these

Forms of Resonance (also called Conjugation)
Simple Carbon Oxygen Double bond
S i r
p t a
G u
a m
u p
A n

1a. Resonance between alternate multiple bond: Carbon double bonds
S i r
p t a
G u
a m
u p
A n

1b. Resonance between alternate multiple bond: Carbon double and triple bonds
S i r
p t a
G u
a m
u p
A n

i r
1c. Resonance between alternate multiple bond: Carbon double and Carbon Oxygen double
bonds S
p t a
G u
a m
u p
A n

2a. Resonance between double bond and lone pair
S i r
p t a
G u
a m
u p
A n

3. Resonance between double bond and +ve charge
S i r
p t a
G u
a m
u p
A n

4. Resonance between double bond and -ve charge
S i r
p t a
G u
a m
u p
A n

5. Resonance between double bond and odd electron (radical)
S i r
p t a
G u
a m
u p
A n

3.0
Stability of Resonating Structures
S i r
and Resonance Energy a
p t
Basics of Organic u
G4
Chemistry am
u p
A n
Anupam Gupta
Revision: Resonance
S i r
p t a
G u
a m
u p
A n

Revision: Forms of Resonance
Simple Carbon Oxygen Double bond
S i r
p t a
u
Resonance between alternate multiple bond: Carbon double bonds
G
a m
p
Resonance between alternate multiple bond: Carbon double and triple bonds
u
A n
Resonance between alternate multiple bond: Carbon double and Carbon Oxygen double
bonds
Revision: Forms of Resonance
Resonance between double bond and lone pair
S i r
p t a
Resonance between double bond and +ve charge
G u
a m
p
Resonance between double bond and -ve charge
u
A n

Revision: Contribution to Resonance Hybrid
S i r
p t a
G u
a m
u p
A n

● Resonance contributors do not have to be equivalent.
S i r
p t a
G u
a m
u p
A n

● Resonance structures do necessarily contribute equally to the resonance hybrid.
S i r
p t a
G u
a m
u p
A n

Stability of Resonating Structures - Complete Octet Rule
i r
a. Structures in which all of the atoms have a complete valence of electrons (i.e., the noble
S
gas structure) are especially stable and make large contributions to the hybrid.
p t a
G u
a m
u p
A n

Stability of Resonating Structures - Complete Octet Rule
Calculation of number of electrons on atoms with formal charges
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
The most stable canonical structure among these is
A. I u p
B. II
A n
C. III
D. All are equally stable

Stability of Resonating Structures - Formal Charges Rule
i r
b. Nonpolar (uncharged) structure are most stable. Charge separation decreases stability.
S
Separating opposite charges requires energy. Therefore, structures in which opposite
t a
charges are separated have greater energy (lower stability) than those that have no
p
charge separation.
G u
a m
u p
A n

Stability of Resonating Structures - Formal Charges Rule
i r
b. Nonpolar (uncharged) structure are most stable. Charge separation decreases stability.
S
Separating opposite charges requires energy. Therefore, structures in which opposite
t a
charges are separated have greater energy (lower stability) than those that have no
p
charge separation.
G u
a m
u p
A n

i r
c. Structures with more covalent bonds are more stable than other structures
S
p t a
G u
a m
u p
A n

i r
d. Structures that carry negative charge on a more electronegative atom and positive
S
charge on less electronegative atom are comparatively more stable.
p t a
G u
a m
u p
A n

Electronegativity
Electronegativity is a concept that describes the tendency of an atom to attract a

shared pair of electrons (or electron density) towards itself.
S i r
p t a
G u
a m
u p
A n

Electronegativity of Carbon atoms
Carbon compound Hybridization

r
Electronegativity value
S i
sp3
p t a2.5
G u
p am
sp2 2.75
n u
A sp 3.25

Important Electronegativity Values of Other atoms
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
The least stable canonical structure among these is
A. I
A n
B. II
C. III
D. All are equally stable
The correct order of stability among these
canonical structures is
A. I > II > III
S i r
B. I > III > II
C. II > I > III
p t a
D. III >I > II
G u
a m
u p
A n

e.
i r
The structures with the least separation of opposite formal charges is more stable
S
p t a
G u
a m
u p
A n

F.
i r
The structures with the large separation of same formal charges is more stable
S
p t a
G u
a m
u p
A n

Among the following, the least stable resonating structure is
A. B.
S i r [IIT-07]
p t a
C. D. G u
a m
u p
A n

The correct stability order of the following resonating structures is
S i r [IIT-09]
p t a
A. (I) > (II) > (IV) > (III)
G u
B. (I) > (III) > (II) > (IV)
a m
C. (II) > (I) > (III) > (IV)
u
D. (III) > (I) > (IV) > (II)
p
A n

S i r
p t a
G u
a m
u p
A n
Among these canonical structures of pyridine, the correct order of stability is
A. (I = V) > (II = IV) > III
B. (II = IV) > (I = V) > III
C. (I = V) > III > (II = IV)
D. III > (II = IV) > (IUnacademy
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S i r
In pyridine electron density is maximum on
p t a
A. 2 and 6
G u
B. 3 and 5
C. 4
a m
D. 3 and 4
u p
A n

3.0
1. Resonance Energy
S i r
2. Aromaticity a
p t
Basics of Organic u
G5
Chemistry am
u p
A n
Anupam Gupta
Revision: Stability of Resonating Structure
S i r
p t a
G u
a m
u p
A n

Effect of Resonance on Stability of Molecule
S i r
p t a
G u
a m
u p
A n

Resonance Energy
S i r
Energy difference between the most stable resonating structure and the hybrid.
p t a
G u
a m
u p
A n

Resonance Energy Calculation
Resonance Energy is calculated using “Heat of Hydrogenation”
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Resonance Energy is calculated using “Heat of Hydrogenation”
S i r
p t a
G u
a m
u p
A n

S i r
t a
Among these compounds, the order of heats of hydrogenation is
p
A. I > II > III
B. III > II > I G u
C. II > I > III
a m
D. II > III > I
u p
A n

Heat of hydrogenation of cyclohexane is -28.6 kcal/mol and that of
benzene is -49.8 kcal/mol. Then resonance energy of benzene will be
A. 46 kcal/mol
S i r
B. 39 kcal/mol
p t a
C. 36 kcal/ mol
D. 30 kcal/mol G u
a m
u p
A n

Diene Heat of hydrogenation
CH2 = CH2 - CH = CH - CH3 -54.1 kcal/mol
I
CH3 - CH = C = CH - CH3 -70.5 kcal/mol
S i r
II
CH2 = CH - CH2 - CH = CH2
t a
-60.2 kcal/mol
p
III
G u
Examine these dienes and their heat of hydrogenations. Now, what will
be the stability order among these dienes?
a m
A. I > II > II
B. II > III > I u p
C. I > III > II
A n
D. II > I > III

Heat of hydrogenation of CH3 - CH = CH2 is -30kcal/mol and resonance
energy of 1,3-butadiene is 3 kcal/mol. What will be the heat of
hydrogenation of 1,3-butadiene?
S i r
A. -63 kcal/mol
B. -57 kcal/mol
p t a
C. -27 kcal/ mol
G u
D. -54 kcal/mol
a m
u p
A n

Aromaticity
S i r
p t a
G u
a m
u p
A n

Rules of Aromaticity
● It must be cyclic and flat (cyclic resonance).

●
●
Every atom in the ring must be conjugated.
The molecule must have [4n+2] electrons in resonance plane. S i r
p t a
G u
a m
u p
A n

Rules of Aromaticity
S i r
p t a
G u
a m
u p
A n

Aromatic Hydrocarbons

●
●
p t a
G u
a m
u p
A n

Aromatic Hydrocarbons - Fused Rings

●
●
p t a
G u
a m
u p
A n

Aromatic Ionic Hydrocarbons
S i r
p t a
G u
a m
u p
A n

Among the following, the number of aromatic compound(s) is
S i r [Adv 2017]
p t a
G u
a m
u p
A n

3.0
Advanced cases of Aromaticity &
S i r
Anti-aromaticity a
p t
Basics of Organic u
G6
Chemistry am
u p
A n
Anupam Gupta
Revision: Aromaticity
● When Resonance Energy is very high in cases of cyclic resonance, it is attributed to

phenomenon of Aromaticity
S i r
p t a
G u
a m
u p
A n

Revision: Rules of Aromaticity

●
●
p t a
G u
a m
u p
A n

Revision: Rules of Aromaticity
S i r
p t a
G u
a m
u p
A n

Revision: Aromatic Hydrocarbons
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Aromatic Heterocyclic Compounds
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
a m
u p
A n

Which of the following compounds is aromatic?
A. B.
S i r
p t a
G u
C. D.
a m
all of these
u p
A n

Oxygen atom of furan is S i r
A. sp3 - hybridized
p t a
B. sp2- hybridized
G u
C. sp-hybridized
D. Not hybridized
a m
u p
A n

Substituted Aromatic Compounds
S i r
p t a
G u
a m
u p
A n

Substituted Aromatic Compounds
S i r
p t a
G u
a m
u p
A n

S i r
p t a
The aromatic character is maximum in which of these three compounds?
A. I G u
B. II
a m
C. III
u p
D. Same in all
A n

Polar Aromatic Compounds
S i r
p t a
G u
a m
u p
A n

S i r
p t a
which of these three compounds? G u
The barrier for rotation about the indicated bonds will be maximum in
A. I
a m
B. II
u p
C. III
A n
D. Same in all

Pi Electron Energy in Aromatic and Anti-Aromatic Compounds
S i r
p t a
G u
a m
u p
A n

S i r
p t a
Which of the following orders is correct for π-electron energy of these cations?
A. I > II
B. II > I G u
C. I = II
a m
p
D. there is nothing like π-electron energy
u
A n

Antiaromatic

●
●
The molecule must have [4n] electrons in resonance plane. S i r
p t a
G u
a m
u p
A n

S i r
Which of these species is anti-aromatic?
p t a
A. I only
B. II only G u
C. III only
a m
D. both II and III
u p
A n

S i r
Which of these species is anti-aromatic?
p t a
A. I only
B. II only G u
C. III only
a m
D. both II and III
u p
A n

S i r
t a
Which of these cyclopropene systems is anti-aromatic?
p
A. I only
B. II only G u
C. III only
a m
D. both II and III
u p
A n

Dimerization of Cyclobutadiene
S i r
p t a
G u
a m
u p
A n

Non-planarity Cyclooctatetraene
S i r
p t a
G u
a m
u p
A n

Anti-aromatic Heterocyclic Compounds
S i r
p t a
G u
a m
u p
A n

Reactions leading to Aromaticity and Antiaromaticity
aromaticity or antiaromaticity in compounds

S i r
Elimination Reactions creating cations (Halogens by Ag+) and anions can cause
p t a
G u
a m
u p
A n

Ease of ionization to produce carbocation an bromide ion under the
treatment of Ag+ will be maximum in which of the following compounds?
A. B.
S i r
p t a
G u
C. D.
a m
u p
A n

P will be
S i r
p t a
A. B.
G u
a m
u p
C.
A n
mixture of A & B D. none of these

S i r
A.
p t a
B. G u
a m
C.
u p
A n
D. mixture of A & B

S i r
A.
p t a
B. G u
a m
u p
C.
A n
D. mixture of A & B

S i r
p t a
A.
G u
B.
a m
u p
C.
A n
D. mixture of A & B

Resonance Energy
S i r
p t a
G u
a m
u p
A n

Resonance Energy
S i r
p t a
G u
a m
u p
A n

S i r
p t a
G u
Among these aromatic compounds the correct order of resonance
energy per ring is
a m
A. I > II > III
u p
B. III > II > I
C. III > I > II A n
D. II > I > III

Which of the following compounds will show highest dipole moment?
S i r [2017]
p t a
G u
A. (I)
a m
B. (II)
u p
C. (III)
D. (IV) A n

The non aromatic compound among the following is:
A. B. S i r [Main 2011]
p t a
G u
C. D.
a m
u p
A n

Which of the following compounds is most reactive to an aqueous
solution of sodium carbonate?
A. B. S i r [2017]
p t a
G u
C. D.
a m
u p
A n

S i r
p t a
G u
Which of the following statements is true about pyrene in addition reactions?
a m
p
A. The central π-bond (encircled) is more reactive than all the peripheral π-
u
bonds
A n
B. The central π-bond is less reactive than all the peripheral π-bonds
C. All π-bond are equally reactive
D. Addition reactions are not possible on this molecule
Among the following, the number of aromatic compound(s) is
S i r [Adv 2017]
p t a
G u
a m
u p
A n


Combined Basics of Organic Chemistry Notes

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A. E2p > Esp3 > Esp2 > Esp > E2s

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A. 2s > 2p sp3 > sp2 > sp

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A. sp3C > sp2C > spC

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A. all three C-atoms are sp2 hybridized

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A. NH3 > H2O > CH4

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O-O oxygen-oxygen single bond

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It is possible, however, to explain properly the properties of many species in terms

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